Vacations Close To Dearborn Station

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Dearborn Station Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,059, price is now $817 per person
$817
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours.

Reviewed on Nov 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,606, price is now $1,102 per person
$1,102
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,576, price is now $1,136 per person
$1,136
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,323, price is now $1,012 per person
$1,012
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $1,080, price is now $829 per person
$829
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
A

Reviewed on Nov 12, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,292, price is now $1,020 per person
$1,020
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was $1,270, price is now $1,044 per person
$1,044
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was $1,134, price is now $936 per person
$936
per person
Dec 21 - Dec 28
just found
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Very clean and comfortable. Valet was helpful and kind

Reviewed on Nov 13, 2026

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Best Lodging Options Near Dearborn Station

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
0.54 km from Dearborn Station
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
0.37 km from Dearborn Station
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
0.91 km from Dearborn Station
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
1.77 km from Dearborn Station
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
0.41 km from Dearborn Station
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
HI Chicago Hostel

HI Chicago Hostel

1.5 out of 5
24 E Ida B Wells Drive Chicago IL
0.47 km from Dearborn Station
Stay at this hostel in Chicago. Enjoy free WiFi, a 24-hour front desk, and 2 meeting rooms. Our guests praise the breakfast and the helpful staff in our reviews. ...
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
0.82 km from Dearborn Station
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
0.42 km from Dearborn Station
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.